United States Court of Appeals For the First Circuit

No. 22-1284

XIOMARA SANTIAGO,

Plaintiff, Appellant,

v.

MUNICIPALITY OF UTUADO,

Defendant, Appellee.

APPEAL FROM THE UNITED STATES DISTRICT COURT FOR THE DISTRICT OF PUERTO RICO

[Hon. Jay A. García-Gregory, U.S. District Judge]

Before

Montecalvo, Lipez, and Thompson, Circuit Judges.

Kenneth Colón, with whom Juan M. Frontera-Suau and Frontera Suau Law Offices, PSC were on brief, for appellant.

Eliezer A. Aldarondo-López, with whom Aldarondo & López-Bras, LLC was on brief, for appellee.

August 22, 2024 THOMPSON, Circuit Judge. The Puerto Rico Municipality

of Utuado hired Xiomara Santiago to be the Deputy Director for the

local Head Start/Early Head Start Program (hereinafter "Head

Start" or "the Program"). Not long after her hire, a mayoral

election changed the town's administration and the new chief exec

terminated Santiago's employment. Claiming her dismissal violated

her Fourteenth Amendment due process rights and was the result of

political discrimination in violation of her First Amendment

rights, Santiago sued the Municipality and sought a preliminary

injunction to get her job back. After the district court held a

series of hearings on Santiago's motion -- four days of testimony

between May 17 and July 2, 2021 from three witnesses -- it

ultimately denied her request, concluding she had not shown a

likelihood of success on the merits of either claim.1 Santiago

now appeals the district court's decision, contending its

conclusion was an abuse of discretion. For the reasons set forth

herein, we affirm.

Background

With the basic scene in place, we now turn to the record

details that are relevant to the claims and arguments at issue on

appeal, pulling out facts from the testimonies provided by

1A magistrate judge presided over the hearings and issued a Report & Recommendation which the district judge ultimately adopted in its entirety over Santiago's objection.

- 2 - Santiago, the new mayor of Utuado, and Head Start's Human Resources

Director, and also from the documents received into evidence during

the hearings. We present the details in chronological order to

best summarize the sequence of events leading up to Santiago's

termination and this litigation which followed. Our chronological

approach means we shift perspectives between witnesses and

documentary evidence a few times. Where certain details aren't

needed to paint the backdrop prior to delving into the merits of

Santiago's claims, we hold those parts of the backstory until our

discussion of the relevant argument when the additional context

will be helpful. We kick things off with some information about

Santiago herself and her start as Head Start's Deputy Director.

Plaintiff Xiomara Santiago holds a bachelor's degree in

Pre-School Education but worked as the Director of Landscaping and

Recycling for the Municipality of Utuado for five years from 2013

until 2018. She next transitioned into the early education field

teaching pre-school for a private company called Urban Strategies

in the Municipality of Ponce. Following her teaching stint, in

March 2020 Santiago successfully applied for the position of Deputy

Director at Head Start for the Municipality of Utuado.

The posting for that position included the following

minimum requirements and application details: (1) a bachelor's

degree in Business Administration or Education; (2) three years of

Head Start experience; (3) one year in a similar management

- 3 - position; and (4) English language proficiency (including

speaking, reading, and writing). To apply, the posting instructed

candidates to submit a college credit transcript, a diploma, a

certificate of Good Conduct and/or Criminal Record, and a document

certifying compliance with filing tax returns for the prior four

years. The posting also clearly stated that "[t]he candidate must

meet the minimum requirements before the closing date and provide

evidence of [all] documents stipulated in the vacancy

announcement[]" and that "incomplete applications . . . or

applications submitted after the closing date" would not be

considered.

Blas Rosado, head of Human Resources at Head Start,

received Santiago's application and forwarded the materials to the

Program's Parents Committee (officially known as the Guideline

Policy Council -- a body comprised of two parents from each Head

Start center within the region who are elected by the parents of

children enrolled in the Program). A subcommittee evaluated all

of the applications and decided whether each candidate met the

requirements from the posted job description. At the preliminary

injunction hearing, Rosado testified that Santiago's application

was complete and that she "fulfill[ed] the required academic

preparation and experience," noting her six years of management

experience "directing and supervising personnel" as well as her

experience as a Head Start teacher when she worked at Urban

- 4 - Strategies. Rosado also testified that the Parents Committee had

agreed she met all the requirements for the position, interviewed

two candidates, and chosen Santiago to advance to the then-mayor

for his okay.

When the Municipality hired Santiago in August 2020 to

be Head Start's Deputy Director, the mayor was Ernesto Irizarry

Salvá, a member of the Popular Democratic Party ("PDP").

Santiago's first months on the job coincided with Utuado's

municipal elections. She demonstrated her interest in the election

process by working as (what she called) a "coordinator for a school

for the [PDP]." In this municipal election cycle, Santiago's

lifelong friend Jorge Pérez Heredia, a member of the New

Progressive Party ("NPP"), ran against Irizarry. One day before

the mid-August primary elections, Santiago received a campaign

text message from Pérez -- a text message pushed out to all the

contacts in his phone. The text included a photo of a sample

ballot with his name checked and a message stating, "I will count

on you tomorrow." Santiago says she ignored this message.

In late October, Pérez sent a text message just to

Santiago which said: "Greetings friend, I only ask you to do

things right, friend." Pérez explained at the preliminary

injunction hearing that he sent the message after trying

unsuccessfully to reach Santiago by phone. When Santiago received

the text, she called Pérez, who, according to Pérez, told her he

- 5 - had filed a complaint with the Puerto Rico Police against Rosado

(the Head Start Human Resources director and a leader of the PDP

with Mayor Irizarry), alleging Rosado had engaged in election fraud

by impersonating a NPP official to get mail-in ballots. Pérez

said he did not want to file a complaint against her as well.

According to Pérez, he implored her to "do things right so she

wouldn't get mixed up in those messes," seemingly implying that he

thought she too had engaged in similar election irregularities.

According to Pérez, he was "warning her because she was [his]

friend and [he] didn't want her to be affected." He "wanted her

to do the correct thing and not do the same thing." Santiago, for

her part, testified Pérez "told [her] that there was a list

containing [her] name; that [she] was going to be investigated by

the feds for electoral fraud." Santiago testified that Pérez was

very upset; the tone of his voice hostile as he told her that he

had the list of people being investigated and she was on it. She

felt threatened by the call even though she knew the fraud

accusation was false. After that call, she continued her political

work with the PDP. When the November 3, 2020 election day rolled

around, Pérez defeated Irizarry to become Utuado's new mayor.

Santiago says she never heard anything else about a fraud

investigation after that, and she continued with her Head Start

work.

- 6 - Between election day and January 11, 2021 (when Pérez

got sworn in as mayor), Mayor Irizarry, as allowed by Puerto Rico

law, sought and received permission from the Director of Human

Resources for the Government of Puerto Rico to renew employment

contracts for over 200 Head Start employees whose transitory

services contracts were set to expire on December 30.2

A quick aside to explain Head Start's governance

structure will be useful to an understanding of Santiago's eventual

employment termination. As described during the hearing, Head

Start programs are operated through grants given by the federal

government to a "regulatory concessionaire" or grantee, such as

the Municipality of Utuado. Utuado is the concessionaire for Head

Start in the Municipalities of Utuado, Jayuya, and Adjuntas.

Utuado's management of the Program is "highly regulated" by the

federal government, with the Program's operations overseen by a

2 The timing for these contract renewals fell within the period blacked out by the Puerto Rico Municipal Code for employment appointments, promotions, transfers, demerits, re- classifications, and salary changes. By law, this period starts two months prior to the general election date and ends on the second Monday of the January following the election. See Rodriguez-Marin v. Rivera-Gonzalez,

(1st Cir. 2006) ("In an effort to combat political discrimination, Puerto Rico has an Electoral Moratorium that prohibits certain 'appointments, promotions, demotions, transfers and changes in the category of the employees' for the two months before and after a general election." (quoting

)). Exemptions exist for programs like Head Start that operate on a January 1 - December 31 fiscal year and where the employees' contracts need to be renewed so the services can continue to be provided to the community.

- 7 - regional managing office in New York. Locally, the Program is

governed by a Board of Directors (or Governing Board, as the

witnesses who testified sometimes called it), a five-person body

headed up by the Mayor of Utuado and populated with four other

members, all of whom are to be current municipal legislators. The

Governing Board is responsible for formal appointments and

personnel changes to the top layers of the Program's

administrations (such as the Director, Deputy Director, Fiscal

Specialist, and Program Specialist) and the Parents Committee

managed the administrative and programmatic parts of the Program

(while being kept in the loop when the Governing Board made changes

to the top Head Start leaders).

The federal grant funds for the Program are budgeted

from January 1 through December 31 of each year. Santiago's

employment -- as well as that of all her colleagues -- was subject

to renewal each year because the regional office approved the Head

Start budget for one-year periods only. Santiago's 2021 employment

contract (which Irizarry had renewed prior to his departure)

included several terms and conditions for her re-appointment to

the Deputy Director position.3 As relevant to this case, one

condition of employment was that she met the minimum requirements

3 The record does not include Santiago's initial employment contract which, presumably, covered the period from her start date in August 2020 through December 31, 2020.

- 8 - of the position. An attachment to the contract spelled out the

Deputy Director's duties and responsibilities which, among other

things, included: assisting the Director to plan, direct,

coordinate, supervise, and evaluate the Program's work and

performance; conducting staff orientation meetings; preparing

reports; helping to draft the annual budget; making presentations

to parents, staff, the governing body, and community groups; and

maintaining relationships with schools, agencies, and community

partners. The renewal contract also listed circumstances under

which the Municipality could terminate her employment, including

if she received "a deficient performance evaluation . . . during

the term of the contract," was "unable to perform the tasks for

which she was hired," budget changes, restructuring or

reorganization of the "offices, centers and/or areas," or "any

other extraordinary situation warranting the termination of th[e]

[c]ontract."

Turning again to Pérez. He took his oath of office on

January 11, 2021, and his first month proved somewhat chaotic on

the Head Start front after he learned that the Municipality's

program was in trouble with the managing office in New York. The

Program's problems included drastically lower student enrollment

-- post Hurricane Maria 356 children enrolled versus the 740

children that the program had represented to the managing office.

Also problematic and not reported to the New York office was the

- 9 - closure of several locations for repairs though staff members in

those shuttered facilities were retained on the payroll. The new

mayor also discovered the Program's noncompliance with the grants'

reporting requirements, including financial management of the

grants, all of which sent Pérez scrambling to find and provide

documentation which ultimately saved $5,000,000 in funding from

one grant but resulted in the loss of $12,000,000 from another

grant. During this time, Pérez wrote a letter to the Director of

Head Start, Christian Quiñones-Figueroa, about the problems he had

unearthed. Quiñones-Figueroa quickly responded, first, briefly

addressing the content of the mayor's letter, then announcing that

he would be on sick leave "for several days" after experiencing a

medical emergency, and finally, indicating Santiago would serve as

Acting Director until his return.4 A few days after this exchange,

Mayor Pérez circulated a memo to the Head Start "supervisors" and

"coordinators" announcing Santiago would be serving as Acting

Director until Quiñones-Figueroa could return to work.

In addition to appointing Santiago to Acting Director

(whose authority, at least on paper, expanded to signing all

4 Pérez's letter to Quiñones-Figueroa is not a part of the record but Quiñones-Figueroa's response to Mayor Pérez provides sufficient textual cues for the court to infer that Quiñones- Figueroa's response was, in part, a reaction to the Mayor's letter in which the Mayor had directed Quiñones-Figueroa to cease all repair projects to Head Start facilities and required all staff to return to working in person.

- 10 - documents, including purchase orders, requisitions, and human

resources-related documents) Pérez decided to bring in Manual

Mena, a close friend he'd known for 30 years to whom he refers as

his "second father," as a volunteer with "experience and

knowledge"5 to serve as Pérez's "aide" as Pérez navigated the

issues between Head Start and the managing office in New York. In

a letter to Mena with a cc to the New York office, Pérez wrote

that he was assigning Mena as "In-Charge for the [Head Start] and

[Early Head Start] Program[s] for the Municipality of Utuado,

effective immediately as to provide continuity for Program

processes and compliance with Federal Regu[l]ations." According

to Santiago, she did not benefit from Mena's presence. As she

tells it, during Mena's first weeks at the Program, he met with

her co-workers several times without inviting her, which made her

feel "pushed aside" and like she did not "have a voice or a vote

at work. . . . They took away all my [work] functions. . . . [I]n

fact, they put a deputy, an interim deputy director, and interim

director above me."

One day in late January or early February (none of the

witnesses could remember the precise date), Pérez held a three-

hour meeting with a dozen or so Head Start managers and

coordinators from various departments to figure out how to resolve

The record does not, however, explain what experience or 5

knowledge Mena brought to the table.

- 11 - the financial reporting issues with the managing office before the

February 28 deadline the New York office had imposed. Throughout

the meeting, Pérez asked Santiago many general questions about the

status of approximately twenty projects, as well as about proposals

and budgets, but she was unable to answer any of the questions.

That was so, Santiago says, because Quiñones-Figueroa "was out on

sick leave and those questions that I could not answer because at

the time I did not have the information." During this meeting

Pérez also learned that Santiago did not have access to the three

electronic databases with information and data about the projects

about which he was inquiring, and Santiago could not tell him why

Quiñones-Figueroa had allowed some staff to work from home and

collect their pay while other staff members were not allowed to

work remotely. Nor could she shed any light on a new employee

supposedly hired on December 31 to fill a fiscal position.

At some point after this meeting, Pérez showed up at

Santiago's office alone. Santiago reported he seemed upset and

was looking for Rosado's office. Admittedly nervous, Santiago

tearfully told him she thought Mena was "going to get [Pérez] into

a lot of trouble" and that she "was already feeling very bad

already because . . . [t]hey were pushing [her] aside and they

were doing things behind [her] back." She reported that Pérez

"remained silent" and "didn't do anything" before leaving her

office for Rosado's.

- 12 - Santiago's termination followed shortly thereafter.

According to Pérez, Santiago's inability to answer any of the

questions he asked at the staff meeting "showed [him] that [she]

lacked any knowledge of the essentials [of] Head Start's

administrative operations or was obstructing the new

administration efforts to obtain the status and continue with a

healthy operation." Rosado testified that the decision to

terminate one of the top positions at Head Start, including the

Deputy Director, had to be approved by the Program's Governing

Board and that the Parents Committee had to be notified. At a

monthly Board of Directors meeting held on February 11, Pérez

discussed his concerns about Head Start and asked the Board to

terminate Santiago. According to Pérez, he had only decided the

morning of the meeting to ask the Board to take this personnel

action. In his hearing testimony, he told the district court that

he decided to terminate Santiago's contract for several reasons:

(1) because, when probed, she did not have a plan to face Head

Start's current crisis of enrollment and problems with financial

reporting; (2) she lacked the experience or knowledge to fulfill

the responsibilities of her role; (3) her position as Deputy

Director was not needed given the impact of COVID-19 on the demand

for services and he was working out how many staff employees the

Program would ultimately need to dismiss given the significant

drop in enrollment; and (4) she was not proficient in English when

- 13 - this had been one of the minimum requirements for the position and

she had attested in her job application that she spoke or wrote in

English.6 In Pérez's eyes, this lack of language proficiency, in

particular, resulted in the mis-entering of program data and the

subsequent jeopardy and loss of Head Start grant funds. In a radio

interview Pérez gave for a local radio station in early March,

amidst a discussion of the problems at Head Start he had inherited

when he took office, he stated that Santiago had been hired without

proper qualifications at a time when the Program couldn't justify

hiring a Deputy Director under the governing regulations due to

flagging enrollment.

After the February 11 Board meeting but prior to Santiago

receiving word that she was to be dismissed from her position,

Mena wrote a memo to all staff announcing that another Head Start

employee now had the exclusive authority to sign all reports,

documents, certifications, etc., effectively removing Santiago's

authority to sign documents as Acting Director on Quiñones-

Figueroa's behalf while he was on leave.

On February 26, Santiago received notice of her

termination via a letter hand delivered to her by the

Municipality's Human Resources Director. The letter stated that

"[t]he Governing Board, at a meeting held on February 11th of 2021

6 When Santiago testified at the hearing she said she could speak some English, with help.

- 14 - and upon my request as Mayor and President of [the Governing]

Board, unanimously removed and dismissed (you as) Deputy Director

of the Head Start Program, effective Friday, March 5th of 2021."

In the week following her termination, several big

changes occurred at Utuado's Head Start Program. For one,

Quiñones-Figueroa resigned as Director. For another, between the

first day of the preliminary injunction hearing (May 17) and the

second day (June 9), Pérez dismissed 31 additional employees, most

of whom had been appointed by the former mayor. While the

Municipality eventually hired a new Director and a Fiscal

Specialist, it did not hire another Deputy Director, effectively

eliminating the position.

In March 2021, Santiago initiated this litigation by

filing her verified complaint against the Municipality of Utuado,

alleging political discrimination and due process claims as well

as violations of several commonwealth laws. In her motion for

preliminary injunction, she requested the court order the

Municipality to reinstate her to Deputy Director and to enjoin it

from further violating her rights.7

7 Santiago's motion for preliminary injunction focused primarily on her federal constitutional claims; her claim of rights violations pursuant to the laws and Constitution of the Commonwealth of Puerto Rico were not separately argued as a basis for the injunctive relief she sought, and the district court focused exclusively on the federal constitutional claims.

- 15 - Soon after the conclusion of the fourth and final day of

testimony, the magistrate judge to whom this case had been referred

issued a Report & Recommendation ("R&R") concluding that Santiago

had not shown a likelihood of success on the merits on either of

her constitutional claims and recommending that the district court

deny her motion for preliminary injunction. Santiago objected to

the R&R, contending the magistrate judge failed to address certain

facts and placed the wrong emphasis on others, leading to the wrong

conclusion about Santiago's likelihood of success on her claims.

The district court adopted the R&R in its entirety and denied the

motion, briefly noting that, in her objection, Santiago had simply

rehashed the same arguments that she had put forth in her motion.

This court has jurisdiction over Santiago's

interlocutory appeal pursuant to

(a)(1).

Discussion

Standard of Review and Preliminary Injunction Standard

This court reviews the district court's denial of a

motion for preliminary injunction for abuse of discretion. Ocean

State Tactical, LLC v. Rhode Island,

(1st Cir.

2024); see also Penalbert-Rosa v. Fortuno-Burset,

(1st Cir. 2011) (acknowledging the abuse-of-discretion

standard of review for denial of requested injunctive relief in a

political discrimination claim but deferring to discussion of Rule

12(b)(6) motion to dismiss). Using this deferential standard,

- 16 - "[w]e review the district court's factual findings for clear error

and its legal conclusions de novo." Ocean State Tactical, LLC,

(alteration in original) (internal quotation marks

omitted) (quoting Together Emps. v. Mass Gen. Brigham Inc.,

(1st Cir. 2022)). We must conclude an abuse of

discretion occurred when a district court "base[s] its ruling on

an erroneous view of the law or on a clearly erroneous assessment

of the evidence." Joseph v. Lincare, Inc.,

(1st

Cir. 2021) (quoting Highmark Inc. v. Allcare Health Mgmt. Sys.,

Inc.,

, 563 n.2 (2014)).

When a party seeks a preliminary injunction, the

district court considers four long-established elements: (1) "the

probability of the movant's success on the merits" of their

claim(s); (2) "the prospect of irreparable harm absent the

injunction"; (3) "the balance of the relevant equities (focusing

upon the hardship to the movant if an injunction does not issue as

contrasted with the hardship to the nonmovant if it does)"; and

(4) "the effect of the court's action on the public interest."

Rosario-Urdaz v. Rivera-Hernandez,

(1st Cir.

2003); see Me. Forest Prods. Council v. Cormier,

(1st Cir. 2022). The movant's likelihood of success on the merits

is the element that "weighs most heavily in the preliminary

injunction calculus," Cormier,

(quoting Ryan v. U.S.

Immigr. & Customs Enf't,

, 18 (1st Cir. 2020)).

- 17 - Fourteenth Amendment Due Process Claim

The district court concluded Santiago was not likely to

succeed on the merits of her due process claim because her initial

hire to Head Start was contrary to Puerto Rico law and, as a

result, she did not have the requisite property interest in her

employment. Santiago puts forth only one argument challenging

this conclusion: She says the district court applied the wrong

Puerto Rico law when it drew this conclusion and that the correct

law would have yielded a different conclusion. As we explain

below, however, her argument is waived. To make our holding clear,

it will be helpful to start with the broad principles for such a

due process claim in the employment context and describe the

district court's reasoning behind its conclusion.

The Fifth and Fourteenth Amendments to the United States

Constitution prohibit the deprivation of property by the federal

or state government without due process of law. U.S. Const. amend.

V, amend. XIV. In the workplace arena, "[t]he Constitution affords

procedural due process protections to government employees who

possess a property interest in continued public employment,"

Casiano-Montañez v. State Ins. Fund Corp.,

(1st

Cir. 2013) (citing Cleveland Bd. of Educ. v. Loudermill,

(1985)), meaning that, "[u]nder the Fourteenth Amendment,

a public employee who possesses a property interest in continued

employment cannot be discharged without due process of law,"

- 18 - Gonzalez-De Blasini v. Fam. Dep't,

(1st Cir. 2004).

A due process claim will fail, however, if the plaintiff cannot

first establish they have a protected property interest in the

employment position in question. García-González v. Puig-Morales,

(1st Cir. 2014). "Property interests are creatures

of state law, and under the laws of Puerto Rico, public employees

who lawfully hold career positions have a protected property

interest in continued employment in those positions." Casiano-

Montañez,

(citing Costa-Urena v. Segarra,

(1st Cir. 2009)). That said, "[e]mployees whose hiring

contravene[s] Commonwealth laws and regulations . . . are not

vested with a property interest in their career positions."

(citing Costa-Urena,

). "'Their career appointments

are null and void ab initio' and no due process protections

attach."

(cleaned up) (quoting Kauffman v. P.R. Tel. Co.,

(1st Cir. 1988)). This court has also acknowledged

that transitory employees working pursuant to a contract with a

specific term of employment have a property interest in their

employment during the term of the contract but not beyond the

expiration of the fixed term of the contract.8 See Borges Colón

8 We have previously explained the distinctions between types of municipal employee classifications as follows: "(1) regular employees, occupying permanent or career municipal positions, (2) transitory employees, appointed without the usual personnel screening procedures (e.g., postings and competitive examinations), but subject to periodic renewals at the expiration

- 19 - v. Román-Abreu,

, 10–11, 18 (1st Cir. 2006); Nieves-

Villanueva v. Soto-Rivera,

(1st Cir. 1997);

Acevedo-Diaz v. Aponte,

, 65 n.1 (1st Cir. 1993). For

these types of employees, "[s]tate statutory law is [but one]

source of 'property' interests in employment. For procedural due

process purposes, it is well settled that an employee's 'property

right' in her job may be established by contract." See Rivera-

Flores v. P.R. Tel. Co.,

, 750 & n.7 (1st Cir. 1995)

(citation omitted). Both the district court and the parties

proceeded as if Santiago, as a transitory employee, had a property

interest in her position.

Even so, the district court concluded Santiago had not

demonstrated a likelihood of success on the merits of her due

process claim because it determined she should never have been

appointed to the Deputy Director position in the first place. The

district court concluded Santiago's appointment to the Deputy

Director position had been contrary to the merit principle

reflected in Puerto Rico Law No. 107-2020 applicable to hiring

of their fixed terms, and (3) contractual workers, hired for fixed terms under federally funded programs (e.g., HUD) administered by the City." Acevedo-Diaz v. Aponte,

, 65 n.1 (1st Cir. 1993) (internal quotation marks omitted). The Municipality hired Santiago after she applied for a job that had been posted and her employment contract for the federally funded Head Start program is titled "Transitory Services Contract," indicating that the line between transitory and contract employees may in fact be perforated, with some employees falling into both categories at the same time.

- 20 - (more on this law in a moment) because she had not met the minimum

requirements for the Deputy Director position. As the district

court reasoned, on the March 2020 closing day for applications to

the position, Santiago submitted only a partially completed

application -- demonstrated by the July 2020 date reflected on two

of the required documents for a complete application listed on the

job posting (the "[c]ertificate of [g]ood [c]onduct and/or

[c]riminal [r]ecord" and "[c]ompliance with the applicable

provisions of the Income Tax Act, as amended, regarding the filing

of tax returns for the four (4) years prior to the application").

The district court also explained that Santiago's apparent lack of

knowledge about some "fundamental operational topics . . . .

bolster[ed] the Municipality's contention that [she] was not

qualified to hold the position" and therefore could not have the

requisite property interest in her employment contract to win a

due process claim.

On appeal, Santiago insists she did have a property

interest in her employment, one created by the renewed transitory

contract, and the Municipality deprived her of this interest when

it summarily terminated her employment two months into the

contract's term. In her objection to the R&R, Santiago challenged

the magistrate judge's conclusion regarding the incomplete

application but she does not press that same argument on appeal.

Instead, she debuts an argument that the district court applied an

- 21 - incorrect Puerto Rico law when it concluded that her initial

appointment as Deputy Director was unlawful because, according to

her, the law on which the district court relied (Law No. 107-2020)

did not come into effect until a few weeks after her initial

appointment. The district court should instead, says Santiago,

have applied federal regulations governing Head Start and Act 81

(a law which was either partially or completely repealed when Law

No. 107-2020 went into effect). Santiago contends she met the

minimum requirements for the Deputy Director position when she was

initially hired and that her appointment complied with Puerto Rico

law, including its "merit principle," as well as with the Head

Start regulations.9 And because she has a cognizable property

9 A quick word about each of these laws and the "merit principle." The district court, citing Law No. 107-2020, stated that "the human resources recruitment system of municipalities is governed by the merit principle so as to promote excellence in public service based on equity, justice, efficiency, productivity, and without discrimination on the basis of, among others, political ideals." See Article 2.042 of the Puerto Rico Municipal code, Puerto Rico Law Number 107-2020, as amended, 21 P.R. Laws Ann. §§ 7001 et seq. ("Law No. 107-2020") and specifically 21 P.R. Laws Ann. § 7231.

Act 81 (from the Autonomous Municipalities Act of 1991) provided in part that

[t]he municipal public service shall be governed by the merit principle to ensure that those who serve the Municipal Government are the fittest. The Municipal Personnel service shall ensure that all career employees of the municipality shall be selected, trained, promoted, retained and treated with consideration of their merits and capability with regard to their employment, without any discrimination for race, color,

- 22 - interest in her transitory employment contract for the duration of

its tenure, Santiago leans on her contention that she was afforded

no due process rights adjacent to her termination, i.e., she was

given no specific reason for her dismissal nor any opportunity to

contest it. As a result, she says, the district court's conclusion

that she had no likelihood of success on the merits of her due

process claim was an "abuse[ of] its discretion."

A threshold obstacle stands in the way of Santiago's

argument. As we noted and as the Municipality correctly counters

in its brief, Santiago is raising this wrong-law-applied argument

for the first time on appeal. She did not contradict the

Municipality's assertion, say for instance, by filing a reply brief

to protest this lack of preservation asseveration. And our review

of the record reveals she did not mention -- in either her written

sex, birth, age, social origin or condition, nor political or religious beliefs.

1991 Laws of Puerto Rico 570-71. Act 81 defined the merit principle as the "concept on which basis all public employees shall be selected, promoted, retained and treated in all matters concerning their employment based upon their capability and without discrimination." Aponte-Ramos v. Álvarez-Rubio,

(1st Cir. 2015) (quoting P.R. Laws Ann. § 1461(42)).

According to the Municipality's briefing, "[o]n August 13, 2020, the Puerto Rico Legislature abrogated the Law of Autonomous Municipalities by way of the Municipal Code, 21 P.R. Laws Ann. § 7001, et seq." The Municipality also states that, "[l]ike the Autonomous Municipalities Act, the more recent statute now governs the organization, administration and operation of Puerto Rico municipalities. A significant amount of the provisions in the old statute remained unchanged."

- 23 - or oral arguments to the district court -- Act 81 or the federal

regulations governing Head Start, even though the Municipality

discussed the asserted applicability of Law No. 107-2020

throughout its written opposition to the motion for preliminary

injunction. Nor did she object to the R&R on this basis to the

district judge. As a result, we deem the argument waived. See

Marcano-Martínez v. Cooperativa de Seguros Múltiples de P.R.,

(1st Cir. 2021) ("Delay in raising arguments wastes

time and money; absent unusual circumstances, arguments raised for

the first time on appeal should fail almost automatically.").

We would usually say no more on a waived issue, but there

is one additional important point to make because, had Santiago

not waived her argument, our consideration of its merits would

have been stymied by Santiago's failure to provide us with a

certified translation of Law No. 107-2020. We explain. Santiago

alleges in her complaint that her initial contract started on

August 1, 2020, and she argues that, with Law No. 107-2020 coming

into effect on August 14 of that year, Act 81 governed her initial

hire (as well as how she -- in her mind -- definitely met the

requirements under Act 81, including pursuant to the federal

regulations governing Head Start). There is, however, no evidence

in the record to prove her precise hire date. All we know is she

submitted her application on the deadline in March and her hiring

process completed sometime in August. This means that each law

- 24 - may have been in effect over the course of her hiring process and

Law No. 107-2020 was certainly in place when she and the

Municipality signed her 2021 employment contract. Add to this

that even if we did know with certainty that one law was in place

over the other, Santiago has not told us how Act 81 substantively

differs from Law No. 107-2020 (if at all in a meaningful way when

both laws seem premised on the merit principle -- Santiago herself

acknowledges the merit principle as the basis for Act 81), or how

application of her preferred law would change the outcome. All

this to say that any consideration of Santiago's arguments on the

merits would need to include an examination of both laws to suss

out the differences between the two, but we would be stuck at the

gate because the new law has yet to receive an official translation

into English, and Santiago did not provide a certified translation

for our review. See 1st Cir. L.R. 30(e).

With that, we move on to Santiago's political

discrimination claim.

First Amendment Political Discrimination Claim10

Santiago challenges the district court's conclusion that

she had not shown political animus drove the Municipality's

There is no doubt that a former employee can have a valid 10

claim for political discrimination under the First Amendment even when there is no valid or meritorious claim for a due process violation. See Acevedo-Diaz,

n.1 ("While their lack of a property interest in their employment positions generally precludes due process claims for a politically discriminatory

- 25 - decision to terminate her employment. As with Santiago's due

process claim, it will be helpful to start our discussion of her

political discrimination claim by setting forth some broad legal

principles. "Government officials are forbidden by the First

Amendment from taking adverse action against public employees on

the basis of political affiliation, unless political loyalty is an

appropriate requirement of the employment." Ocasio-Hernández v.

Fortuño-Burset,

(1st Cir. 2011) (citing Rutan v.

Republican Party of Ill.,

(1990)). A plaintiff

claiming political discrimination establishes a prima face case by

proving four elements: "(1) that the plaintiff and defendant have

opposing political affiliations, (2) that the defendant is aware

of the plaintiff's affiliation, (3) that an adverse employment

action occurred, and (4) that political affiliation was a

substantial or motivating factor for the adverse employment

action."

(quoting Lamboy-Ortiz v. Ortiz-Vélez,

(1st Cir. 2010)); Hatfield-Bermudez v. Aldanondo-Rivera,

(1st Cir. 2007) (referring to these four elements as

the prima facie case); Peguero-Moronta v. Santiago,

,

48 (1st Cir. 2006). "Proving that political affiliation was a

substantial or motivating factor in an adverse employment decision

requires more than 'merely juxtaposing a protected characteristic—

dismissal, First Amendment discrimination claims are not precluded."); see also Borges Colón, 438 F.3d at 11.

- 26 - someone else's politics—with the fact that the plaintiff was

treated unfairly.'" Peguero-Moronta, 464 F.3d at 45 (cleaned up)

(quoting Padilla–García v. Guillermo Rodríguez,

, 74

(1st Cir. 2000)). "The Supreme Court has cautioned that the mere

fact that an adverse action was taken after an employee exercises

First Amendment rights is not enough by itself to establish a prima

facie case." Id. (citing Bd. of Cty. Comm'rs v. Umbehr,

(1996)).

As the district court recognized, the first three

elements are not in dispute here: Santiago supported the PDP;

Mayor Pérez, who is a member of the NPP, knew she supported the

PDP; and she was terminated before the end of her employment

contract. The district court concluded Santiago hadn't provided

enough evidence to show the fourth element -- that "political

discriminatory animus was at the center of the decision to

terminate her employment" -- and therefore had not shown likelihood

of success on a prima facie claim of political discrimination.

On appeal, Santiago asserts she did provide "specific

facts necessary" to show beyond mere speculation that her political

affiliation with the PDP was a substantial or motivating factor

for her termination, meaning that political discriminatory animus

drove the decision to end her employment with Head Start and the

district court abused its discretion by concluding otherwise. As

support from the record, she highlights Pérez's contact with her

- 27 - prior to the election (the missed phone call, the text, and phone

conversation), Pérez's withdrawal (prior to her termination) of

her authorization to sign official documents on behalf of the Head

Start Director who was out on sick leave, Pérez announcing his

longtime friend and mentor as "in charge" of Head Start in a

volunteer capacity and who immediately took actions to usurp her

authority as Deputy Director, Pérez's decision to terminate her

employment without -- Santiago says -- the required approval of a

legally formed Governing Board or the Parents Committee,11 and

Pérez's comments during a radio interview given a few weeks after

11Some additional details from the record are needed here to fully articulate what Santiago has written in her briefing to us on this point. Santiago contends (as she did below) that the Governing Board was not properly formed at the time of the February 11 meeting when Mayor Pérez sought the Board's permission to terminate her contract and dismiss her because the new members of the Board were not "duly appointed" pursuant to "Ordinance 29." At the hearing, Mayor Pérez testified he had appointed new members to the Governing Board after he took office and that two of these members were municipal legislators and two of these members were "from the community" and current public sector employees. Mayor Pérez acknowledged that Ordinance 29 of the Municipality of Utuado specified that the Head Start Governing Board members had to all also be municipal legislators but that his administration was in the process of amending this Ordinance because the soon-to-be updated Municipal Code (see note 9, supra) allowed changes to the Board's composition and he "decided to constitute the Board according to the . . . new Municipal Code." Santiago also argued that the Parents Committee had to approve her dismissal but that Pérez admitted he had not sought their approval. Santiago does not provide any regulations stating this requirement, and we note that Rosado testified that the Parents Committee merely needs to be notified of any personnel changes (and they were by the cc to them on Santiago's letter of termination). In Santiago's eyes, this all provides circumstantial evidence of discriminatory animus on Pérez's part.

- 28 - her dismissal."12 Santiago does not, however, attempt to or

actually connect the dots to tie any of these just recited factual

allegations to our case law in order to support her argument that

this was sufficient to show a likelihood of success on the merits

that her political support for the PDP was a substantial factor in

Pérez's decision to terminate her employment.13

The Municipality counters that Santiago's appellate

arguments reflect her disagreement with the district court's view

of the evidence but that the district court's analysis was correct,

lacking clear error or any abuse of discretion. The Municipality

argues (and Santiago acknowledges) that the short span of time

between Pérez taking office and Santiago's termination is not

12A little additional context will be helpful here too. In the March 10 radio interview mentioned briefly supra, the radio host asked Pérez to respond to criticism in a press release from another political party's legislator about Pérez's response to the Head Start crisis with the managing office (including bringing Mena into the fold) and the way in which Pérez was changing the composition of and selection process for the members of the Program's Governing Board. Part of Pérez's response included a comment that the legislator who had issued the accusatory press release was actually a supporter of the former mayor and that she and his party "were carrying [Irizarry's] briefcase. [He] is no longer there, and they've to get their payback." Pérez also discussed Santiago's dismissal during this interview and because he did she urges that this statement is evidence that political affiliation was a substantial factor in her termination.

13 The single case she cites amidst her discussion of the facts she believes are in her favor is focused on whether a deviation from the usual termination procedure was evidence of pretext for a retaliation claim, not a political discrimination claim as we have before us. See Kouvchinov v. Parametric Tech. Corp.,

(1st Cir. 2008).

- 29 - sufficient on its own, and it refutes each of the pieces of

evidence Santiago argued should have tipped her across the line

from speculative to indicative of likelihood of success on the

merits. For example, it says that the text messages sent during

the campaign season as well as the phone conversation did not show

his political animus but instead, his disdain for the acts of

electoral fraud he believed had occurred. The radio interview,

says the Municipality, did not show political animus towards

Santiago but frustration at the way the previous administration

had run Head Start. Finally, the Municipality asserts that

Santiago was not terminated as a result of political animus but

because she lacked the minimum requirements for the Deputy Director

position as well as the knowledge required to execute the

responsibilities of the position. As for Santiago's argument that

the Head Start Board was not properly constituted at the time it

approved her proposed termination or that the Parents Committee

was deprived of an opportunity to weigh in, the Municipality points

out that Santiago does not provide any indication that the

approvals from these bodies were a standard operating procedure or

practice at Head Start such that this alleged deviation could be

evidence of animus.14

We note again that Santiago did not avail herself of the 14

opportunity to file a reply brief to counter any of these contentions.

- 30 - In our view, the record does not show that the district

court clearly erred in its interpretation of the evidence before

it or abused its discretion by concluding that Santiago's

affiliation with or support of the PDP was not a substantial factor

in Pérez's decision to terminate her contract mid-term. The only

politically-inflected exchanges between Pérez and Santiago, as far

as the record reveals, are Pérez's text messages to Santiago asking

for her support and warning her to avoid any shenanigans, and his

telephone conversation with her about election irregularities.

But these events occurred months before he took office, and nothing

about his conduct after becoming mayor shows that his actions

towards Santiago were motivated by political ill-will rather than

appropriate managerial considerations.

In the first weeks in his role as mayor, he discovered

Head Start was in quite a bad spot vis-à-vis the managing office

in New York and the events described and documented on the record

reveal the quick steps he tried to take to get to the bottom of

the problem so he could stop the rescission of the grant funds.

That the Head Start Director needed immediate medical leave did

not help Pérez's efforts but he did follow Quiñones-Figueroa's

suggestion and appointed Santiago Acting Director before

discovering, soon thereafter, that it appeared she had neither the

knowledge nor the access to required databases to help pull the

Program out of its troubles. While Pérez, through Mena, rescinded

- 31 - Santiago's authority to execute official, Program-related

documents before notifying her of her dismissal, the record shows

that the memo announcing the change of signatory authority occurred

after Pérez received approval to terminate her contract,

indicating a logical managerial decision even if not tactfully

executed.

To be sure, Santiago's termination letter provided no

explanation for her dismissal, but such lack of notice is not alone

dispositive. To show a likelihood of success on this "substantial

or motivating factor" element, she needs more than a "[m]ere[]

juxtaposi[tion]" of her support for the PDP with any arguably

unfair treatment she experienced in the lead up to and including

her termination. Peguero-Moronta, 464 F.3d at 45 (first alteration

in original). Santiago acknowledges this requirement in her brief

to us. But she has not provided any evidence such as proof of a

highly charged political office atmosphere or evidence of comments

by Pérez or any colleagues at Head Start that the administration

wanted to focus on dismissing or laying off employees who were

known supporters of the PDP. See Borges Colón, 438 F.3d at 11,

18, 22 (highlighting evidence that plaintiff's replacement was

from a different political party, the mayor made comments about

"get[ting] rid" of opposing party supporters who were employed in

the office, and refutation of the stated reason for non-renewal of

plaintiff's employment contract to affirm a jury verdict on a

- 32 - political discrimination First Amendment claim). Moreover, she

makes no argument that the Head Start employees laid off after

Santiago's termination were PDP supporters.

The final problem is that, as we mentioned above,

Santiago hasn't pointed us to any cases indicating that, based on

our law governing political discrimination claims, the district

court made the wrong call about her likelihood of success on the

merits. See United States v. De La Cruz,

(1st

Cir. 2008) (rejecting an appellant's argument in part for not

citing to any cases which specifically supported the articulated

appellate argument and for only citing cases which supported

general propositions relevant to the constitutional issue at

hand). In all, the district court's conclusion that Santiago's

support for the PDP was not a substantial factor in the termination

decision is well-supported by the record and Santiago has not

provided any reasons based on the record or case law to indicate

that the district court abused its substantial discretion.15

15 Santiago also spills some ink arguing that the district judge did not conduct a proper de novo review of the motion for preliminary injunction because the judge incorrectly characterized Santiago's objection to the R&R as a "rehash" of her motion. As Santiago herself cites, Federal Rule of Civil Procedure 72(b) and

(b)(1) govern the district judge's review of a "properly objected to" "magistrate judge[] disposition[,]" but the rule and statute only instruct that the district judge's review is de novo and that the judge has a range of options, including to "accept, reject, or modify the recommended disposition; receive further evidence; or return the matter to the magistrate judge with instructions." The Rule does not instruct district judges

- 33 - Conclusion

Given our conclusions above about Santiago's challenges

to the district court's conclusions about the likelihood of success

on the merits of her two claims, we need not explore the other

factors required to secure a preliminary injunction. The denial

of Santiago's motion for preliminary injunction is affirmed. Each

side to bear their own costs.

that they must explain their reasoning at all or in any degree of detail. Here, the district judge stated that, after considering Santiago's objections and reviewing the record de novo, he concluded the R&R was "well-grounded in both fact and law" and adopted the R&R in its entirety for the reasons stated within the R&R. As with Santiago's arguments before us on her two constitutional claims, her objection to the R&R is devoid of any attempt to demonstrate the R&R reflected the application of the wrong laws governing the two claims or that, pursuant to our governing case law, the R&R drew the incorrect legal conclusions regarding her likelihood of success on the merits of her claims. Beyond general statements of law, the objection simply argued the facts. After reviewing the record and considering the case law, we conclude there is no indication that the district judge misread the record or misapplied the applicable law.

- 34 -